期刊
TETRAHEDRON
卷 63, 期 37, 页码 9221-9228出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2007.06.054
关键词
bismuth(III) salts; epoxysteroids; halohydrins; beta-hydroxy nitrates
The ring opening of various epoxides was achieved under mild conditions using bismuth(III) salts. Halohydrins and beta-hydroxy nitrates were efficiently obtained from the corresponding 5 alpha,6 alpha-, 2 alpha,3 alpha-, and 5 beta,6 beta-epoxysteroid using BiCl3, BiBr3 or Bi(NO3)(3) center dot 5H2O. Considerations about the probable reaction mechanism are provided. 2D homo- and heteronuclear correlation NMR spectroscopic techniques were used to unequivocally demonstrate the trans-diaxial nature of the epoxide ring opening. (c) 2007 Elsevier Ltd. All rights reserved.
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